Sodium hydride → 2-Hydroxybenzo(b)thiophene-3-carboxamide

HRID 2231289Notes

Reaction equation

HRID 2231289 reaction equation
[S:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[CH2:3][C:2]1=[O:10].C1([NH:17][C:18](=O)[O-:19])C=CC=CC=1.[H-].[Na+]>CN(C)P(=O)(N(C)C)N(C)C>[OH:10][C:2]1[S:1][C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[C:3]=1[C:18]([NH2:17])=[O:19]

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 591560Benzo[b]thiophen-2(3H)-oneHCID 21896570Phenylcarbamate

Product 1

HCID 142579342-Hydroxybenzo(b)thiophene-3-carboxamide

Reagents, catalysts & solvents 1

HCID 12679HexamethylphosphoramideSolvent

Procedure

To a stirred mixture of benzthiophene-2-one (1.50 g, 0.01 m), phenylcarbamate (1.4 g, 0.01 m), and hexamethylphosphorictriamide (2.2 ml) at 5° C. is added sodium hydride (0.24 g, from 0.4 g 60% mineral oil dispersion), and the resultant mixture stirred at ambient temperatures for 5 hours. The volatiles are removed under high vacuum, and the residue triturated well with hexane and then with water to yield 2-hydroxybenzo(b)thiophene-3-carboxamide.

Workup

  1. customThe volatiles are removed under high vacuum
  2. customthe residue triturated well with hexane

Sources & evidence

ORD record
ord-cc718fd0a37540408b5a23c2d9de603e
Source dataset
uspto-grants-1988_11
Patent number
US04782080

Reaction notes

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